US4528415A
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Ethylene dimerization
Assignee: Phillips Petroleum Co
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Filing: 1984-08-20
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Granted: 1985-07-09
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Expires: 2004-08-20
Abstract
Abstract A novel ethylene dimerization catalyst is provided consisting essentially of a nickel compound, a phosphine compound, and an acidic compound. In addition, an improved ethylene dimerization process is provided which comprises contacting ethylene with the novel catalyst composition present, in an effective solvent, at a temperature from about 0° C. to about 200° C. As a result of the inventive precess, high catalyst productivity and good selectivity to the desired dimerized product, 1-butene, is obtained.
Inventors
- 👤 Ronald D. Knudsen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:36
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/02; B01J31/0215; B01J31/0225; B01J31/0227; C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; B01J2231/00; B01J2231/20; B01J2231/30; B01J2231/32; B01J2231/323; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J31/22; B01J31/2282; B01J31/2291; B01J31/2295; C07C2531/00; C07C2531/02; C07C2531/025; C07C2531/16; C07C2531/22; C07C2531/24; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/52
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
207 words
A process for the oligomerization of ethylene which comprises contacting said ethylene with a catalyst composition in the liquid phase present in at least one solvent selected from the group consisting of: (i) an aromatic hydrocarbon of the formula ##STR3## wherein each R"' independently represents a C 1 to C 6 alkyl radical and n is 0, 1, 2, 3, or 4; and (ii) an alcohol of the formula (R iv ) 3 COH wherein each R iv independently represents H or a C 1 to C 12 alkyl, cycloalkyl, aryl, alkaryl, or aralkyl radical; the catalyst consisting essentially of: (a) at least one nickel compound selected from the group consisting of: bis(1,5-cyclooctadiene)nickel(0); bis(tricyclohexylphosphine)nickel(0); (cyclododecatriene)nickel; and bis(ethylene)(dicyclohexylphosphine)nickel; (b) a phosphine compound of the formula PR 3 wherein each R independently represents H or a C l to C 20 hydrocarbyl radical with the proviso that any alkenyl substitution be at least 3 carbon atoms removed from the phosphorus atom and at least one R is not H; and (c) an acidic compound selected from the groups consisting of (i) a sulfonic acid of the formula R'SO 3 H wherein R' is H, or a fluorinated or nonfluorinated alkyl, aryl, alkaryl, or aralkyl radical with 1-10 carbon atoms.
Claim 2
Dependent Claim
207 words
A process for the oligomerization of ethylene which comprises contacting said ethylene with a catalyst composition in the liquid phase present in at least one solvent selected from the group consisting of: (i) an aromatic hydrocarbon of the formula ##STR3## wherein each R"' independently represents a C 1 to C 6 alkyl radical and n is 0, 1, 2, 3, or 4; and (ii) an alcohol of the formula (R iv ) 3 COH wherein each R iv independently represents H or a C 1 to C 12 alkyl, cycloalkyl, aryl, alkaryl, or aralkyl radical; the catalyst consisting essentially of: (a) at least one nickel compound selected from the group consisting of: bis(1,5-cyclooctadiene)nickel(0); bis(tricyclohexylphosphine)nickel(0); (cyclododecatriene)nickel; and bis(ethylene)(dicyclohexylphosphine)nickel; (b) a phosphine compound of the formula PR 3 wherein each R independently represents H or a C l to C 20 hydrocarbyl radical with the proviso that any alkenyl substitution be at least 3 carbon atoms removed from the phosphorus atom and at least one R is not H; and (c) an acidic compound selected from the groups consisting of (i) a sulfonic acid of the formula R'SO 3 H wherein R' is H, or a fluorinated or nonfluorinated alkyl, aryl, alkaryl, or aralkyl radical with 1-10 carbon atoms.
Claim 3
Dependent Claim
20 words
A process according to claim 1 carried out at a temperature of from about 0° C. to about 200° C.
Claim 4
Dependent Claim
24 words
A process according to claim 1 wherein said solvent is one selected from the group consisting of benzene, toluene, xylenes, trimethylbenzenes, ethylbenzenes, and cumene.
Claim 5
Dependent Claim
11 words
A process according to claim 1 wherein said solvent is toluene.
Claim 6
Dependent Claim
24 words
A process according to claim 1 wherein said solvent is one selected from the group consisting of ethanol, 2-pentanol, t-butanol, iso-butanol, 2-butanol, and 2-hexanol.
Claim 7
Dependent Claim
11 words
A process according to claim 1 wherein said solvent is 2-pentanol.
Claim 8
Dependent Claim
12 words
A process according to claim 1 wherein said nickel compound is bis(1,5-cyclooctadiene)nickel(O).
Claim 9
Dependent Claim
22 words
A process according to claim 1 wherein said phosphine compound is one selected from the group consisting of triphenylphosphine, tris(4-fluorophenyl)phosphine, and dicyclohexylphosphine.
Claim 10
Dependent Claim
12 words
A process according to claim 1 wherein said phosphine compound is dicyclohexylphosphine.
Claim 11
Dependent Claim
12 words
A process according to claim 1 wherein said acid is p-toluenesulfonic acid.
Claim 12
Dependent Claim
12 words
A process according to claim 1 wherein said acid is trifluoromethanesulfonic acid.
Claim 13
Dependent Claim
38 words
A process according to claim 1 wherein the molar ratio of (b) to (a) of said composition is about 0.5-2.5 to 1 and the molar ratio of (c) to (a) of said composition is about 0.01-10.0 to 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1988-07-08 | 1989-01-07 | 1989-07-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-08 | 1993-01-07 | 1993-07-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-08 | 1997-01-07 | 1997-07-09 | $7700.00 | Window Closed / Lapsed |